Co-reporter:Hong-Hao Zhang and Shouyun Yu
The Journal of Organic Chemistry October 6, 2017 Volume 82(Issue 19) pp:9995-9995
Publication Date(Web):August 21, 2017
DOI:10.1021/acs.joc.7b01425
Radical alkylation of imines with 4-alkyl-1,4-dihydropyridines cocatalyzed by iridium/ruthenium complex and Brønsted acid under visible light irradiation has been achieved. Both aldimines and ketimines can undergo this transformation. Common functional groups, such as hydroxyl groups, ester, amide, ether, cyanide, and heterocycles, can be tolerated in this reaction. A variety of structurally diverse amines (57 examples) have been produced with up to 98% isolated yields using this method.
Co-reporter:Qixue Qin, Yue-Yue Han, Yan-Yan Jiao, Yanyan He, and Shouyun Yu
Organic Letters June 2, 2017 Volume 19(Issue 11) pp:
Publication Date(Web):May 16, 2017
DOI:10.1021/acs.orglett.7b01145
Photoredox-catalyzed difunctionalizations of alkenes with O-acyl hydroxylamine derivatives are described. The solvent tunes the outcome of these reactions. Diamidation and oxidative amidation of alkenes can be achieved in CH3CN and DMSO, respectively. A variety of 1,2-diamidates and α-amino ketones bearing many functional groups are prepared using Ir(ppy)3 as the photocatalyst under visible light irradiation.
Co-reporter:Muliang Zhang, Rehanguli Ruzi, Junwei Xi, Nan Li, Zhongkai Wu, Weipeng Li, Shouyun Yu, and Chengjian Zhu
Organic Letters July 7, 2017 Volume 19(Issue 13) pp:
Publication Date(Web):June 14, 2017
DOI:10.1021/acs.orglett.7b01391
A hydroacylation reaction of alkenes has been achieved employing readily available carboxylic acids as the acyl source and hydrosilanes as a hydrogen source via photoredox catalysis. The combination of both single electron transfer and hydrogen atom transfer steps has dramatically expanded new applications of carboxylic acids in organic synthesis. The protocol also features extremely mild conditions, broad substrate scope, and good functional group tolerance, affording a novel and convenient approach to hydroacylation of alkenes.
Co-reporter:Jian Cheng, Weipeng Li, Yingqian Duan, Yixiang ChengShouyun Yu, Chengjian Zhu
Organic Letters 2017 Volume 19(Issue 1) pp:214-217
Publication Date(Web):December 20, 2016
DOI:10.1021/acs.orglett.6b03497
A relay visible-light photoredox catalysis strategy has been accomplished. Three successive photoredox cycles (one oxidative quenching cycle and two reductive quenching cycles) are engaged in a single reaction with one photocatalyst. This strategy enables formal [4 + 1] annulation of hydrazones with 2-bromo-1,3-dicarbonyl compounds, which functionalizes three C–H bonds of hydrazones. This method affords rapid access to a complex and biologically important pyrazole scaffold in a step-economical manner with high efficiency under mild conditions.
Co-reporter:Hao Wang, Qian Xu, Sheng Shen, and Shouyun Yu
The Journal of Organic Chemistry 2017 Volume 82(Issue 1) pp:770-775
Publication Date(Web):December 12, 2016
DOI:10.1021/acs.joc.6b02509
An efficient and rapid synthesis of multiply substituted quinolines is described. This method is enabled by a three-component cascade annulation of readily available aryl diazonium salts, nitriles, and alkynes. This reaction is catalyst- and additive-free. Various aryl diazonium salts, nitriles, and alkynes can participate in this transformation, and the yields are up to 83%.
Co-reporter:Heng Jiang, Yanyan He, Yuanzheng Cheng, and Shouyun Yu
Organic Letters 2017 Volume 19(Issue 5) pp:
Publication Date(Web):February 16, 2017
DOI:10.1021/acs.orglett.7b00337
Radical alkynyltrifluoromethylation of alkenes with actylenic triflones has been achieved. This radical chain reaction is initiated by a catalytic amount of an electron-donor–acceptor complex composed of Togni’s reagent and N-methylmorpholine. This transformation proceeds under exceptionally mild and operationally simple conditions. A variety of alkenes are compatible in this protocol including aliphatic alkenes, vinyl ethers, enecarbamates, styrenes, and even acrylates, providing diverse β- trifluoromethyl alkynes in good to excellent yields.
Co-reporter:Muliang Zhang;Nan Li;Xingyu Tao;Rehanguli Ruzi;Chengjian Zhu
Chemical Communications 2017 vol. 53(Issue 73) pp:10228-10231
Publication Date(Web):2017/09/12
DOI:10.1039/C7CC05570F
The direct reduction of carboxylic acids to aldehydes with hydrosilane was achieved through visible light photoredox catalysis. The combination of both single electron transfer and hydrogen atom transfer steps offers a novel and convenient approach to selective reduction of carboxylic acids to aldehydes. The method also features mild conditions, high yields, broad substrate scope, and good functional group tolerance, such as alkyne, ester, ketone, amide and amine groups.
Co-reporter:Wenmin Wang;Xiaoyang Sun;Jian Qu;Xiaoyu Xie;Zheng-Hang Qi;Daocheng Hong;Su Jing;Dong Zheng;Yuxi Tian;Haibo Ma;Jing Ma
Physical Chemistry Chemical Physics 2017 vol. 19(Issue 46) pp:31443-31451
Publication Date(Web):2017/11/29
DOI:10.1039/C7CP05936A
The joint computational and experimental efforts reveal that the organic molecule 1,2-diisocyano-4,5-dimethylbenzene (1) acts as both a reactant and a photosensitizer (PS) in a metal-free reaction with perfluoroalkylhalide (2) to produce 2-perfluoroalkyl quinoxalines (3) under visible light. Both the π–π stacking aggregation in crystals and the solvation in various solvents of PS 1 exhibited visible-light absorption at 466 nm in spite of its smaller coefficient than that of the ultraviolet-light absorption. Such an aggregation-assisted visible-light absorption phenomenon is rationalized by theoretical calculations of the condensed-phase properties with the consideration of the explicit polarization effect from the neighboring molecules. Upon irradiation with different wavelengths, the emission colors changed from navy to bright yellow. Fluorescence lifetime measurements show that the emission of 1 comes from its singlet excited state. The aggregation induced emission when excited at 420 nm has a shorter lifetime (0.45 ns) than that of the emission from isolated molecules (2.71 ns) when excited at 381 nm. It is conceived that the aggregation assisted visible light absorption properties may be general in other photo-reactive molecules, such as 1,4-diisocyano-2,5-dimethylbenzene (4), 1,4-dicyanobenzene (5), and 1,4-diisocyanobenzene (6), which are widely used in many photochemical reactions in the absence of any external photosensitizer.
Co-reporter:Xiaodong Liu;Kun Tong;Ai Hua Zhang;Ren Xiang Tan
Organic Chemistry Frontiers 2017 vol. 4(Issue 7) pp:1354-1357
Publication Date(Web):2017/06/27
DOI:10.1039/C7QO00199A
An efficient and rapid protocol for chloroamidation of indoles with sulfonamides and aqueous NaClO has been developed. The reaction completes in less than half an hour at room temperature without any transition metals. Both indoles and sulfonamides can be easily varied with high functional group tolerance. A variety of structurally diverse 3-chloro-2-amidoindoles are prepared with up to 97% yields.
Co-reporter:Muliang Zhang, Yingqian Duan, Weipeng Li, Pan Xu, Jian Cheng, Shouyun Yu, and Chengjian Zhu
Organic Letters 2016 Volume 18(Issue 20) pp:5356-5359
Publication Date(Web):September 30, 2016
DOI:10.1021/acs.orglett.6b02711
The reductive single electron transfer (SET) umpolung amination of aldehyde-derived hydrazones has been developed through visible-light-promoted photoredox catalysis. The ideal transformation of hydrazones into the corresponding hydrazonamide through selective carbon–hydrogen (C–H) bond functionalization represents one of the most step- and atom-economical methods. This SET umpolung strategy features mild conditions and a remarkably broad substrate scope, offering an entirely new substrate class to direct C–H amination.
Co-reporter:Xiaoyang Sun, Wenmin Wang, Yanle Li, Jing Ma, and Shouyun Yu
Organic Letters 2016 Volume 18(Issue 18) pp:4638-4641
Publication Date(Web):August 31, 2016
DOI:10.1021/acs.orglett.6b02271
A halogen-bond-promoted double radical isocyanide insertion with perfluoroalkyl iodides is reported. With perfluoroalkyl iodides as halogen-bond donors and organic bases as halogen-bond acceptors, fluoroalkyl radicals can be generated by a visible-light-induced single electron transfer (SET) process. The fluoroalkyl radicals are trapped by o-diisocyanoarenes to give quinoxaline derivatives. This mechanistically novel strategy allows the construction of 2-fluoroalkylated 3-iodoquinoxalines in high yields under visible-light irradiation at room temperature.
Co-reporter:Yuanzheng Cheng and Shouyun Yu
Organic Letters 2016 Volume 18(Issue 12) pp:2962-2965
Publication Date(Web):May 26, 2016
DOI:10.1021/acs.orglett.6b01301
An electron-donor–acceptor (EDA) complex between Togni’s reagent and a tertiary amine has been introduced. The existence of this EDA complex was supported by NMR titration experiments. The hydrotrifluoromethylation of unactivated aliphatic alkenes and alkynes enabled by this EDA complex has also been developed. This hydrotrifluoromethylation protocol is operationally simple and promoted by a tertiary amine.
Co-reporter:Hui Zhou, Xinzhao Deng, Zhenjun Ma, Aihua Zhang, Qixue Qin, Ren Xiang Tan and Shouyun Yu
Organic & Biomolecular Chemistry 2016 vol. 14(Issue 25) pp:6065-6070
Publication Date(Web):18 May 2016
DOI:10.1039/C6OB00768F
The synthesis of privileged structures, which are potent drug candidates, is an impetus for drug discovery. The construction of heterocyclic framework furo[3,2-c]coumarins using a visible-light promoted photoredox neutral coupling of 3-bromo-4-hydroxycoumarins with commercially available alkynes has been reported. These reactions can be carried out at room temperature under visible light irradiation with good chemical yields. This work presents 17 furocoumarins, 12 of which are new. Three of the newly synthesized compounds show potent cytotoxicity, and one shows moderate acetylcholinesterase inhibitory activity with IC50 values of 2.16 ± 0.13 μM.
Co-reporter:Yue-Yue Han, Heng Jiang, Ruzhi Wang, and Shouyun Yu
The Journal of Organic Chemistry 2016 Volume 81(Issue 16) pp:7276-7281
Publication Date(Web):June 3, 2016
DOI:10.1021/acs.joc.6b00869
A practical approach for the synthesis of tetracyclic pyrroloquinazolines using photoredox strategy has been developed. The visible-light-promoted intramolecular single-electron-transfer process between photocatalyst and N-(2-iodobenzyl)-N-acylcyanamides is considered to be involved in this transformation. Targeted pyrroloquinazoline derivatives (15 examples) are presented in good isolated yields (30%–88%).
Co-reporter:Hao Wang;Yuanzheng Cheng
Science China Chemistry 2016 Volume 59( Issue 2) pp:195-198
Publication Date(Web):2016 February
DOI:10.1007/s11426-015-5528-1
An efficient and practical method is developed for the trifluoromethylation of enamides using Umemoto’s reagent as the trifluoromethylating reagent. These reactions proceeded under visible light irradiation without any photocatalyst at room temperature in good chemical yields.
Co-reporter:Hao Wang and Shouyun Yu
Organic Letters 2015 Volume 17(Issue 17) pp:4272-4275
Publication Date(Web):August 20, 2015
DOI:10.1021/acs.orglett.5b01960
A visible-light-promoted regioselective denitrogenative insertion of terminal alkynes into 1,2,3-benzotriazinones is reported. This mechanistically novel process allows the synthesis of substituted isoquinolones in satisfactory isolated yields (24 examples, 46–84% yield) at room temperature under visible-light irradiation with the assistance of a photocatalyst. The proposed single-electron-transfer pathway was supported by TEMPO trapping, radical clock experiments, and Stern–Volmer analysis.
Co-reporter:Xiao-De An and Shouyun Yu
Organic Letters 2015 Volume 17(Issue 11) pp:2692-2695
Publication Date(Web):May 12, 2015
DOI:10.1021/acs.orglett.5b01096
A one-pot synthesis of phenanthridines and quinolines from commercially available or easily prepared aldehydes has been reported. O-(4-Cyanobenzoyl)hydroxylamine was utilized as the nitrogen source to generate O-acyl oximes in situ with aldehydes catalyzed by Brønsted acid. O-Acyl oximes were then subjected to visible light photoredox catalyzed cyclization via iminyl radicals to furnish aza-arenes. A variety of phenanthridines and quinolines have been prepared assisted by Brønsted acid and photocatalyst under visible light at room temperature with satisfactory yields.
Co-reporter:Qixue Qin and Shouyun Yu
Organic Letters 2015 Volume 17(Issue 8) pp:1894-1897
Publication Date(Web):April 8, 2015
DOI:10.1021/acs.orglett.5b00582
A visible-light-promoted C(sp3)–H amidation and chlorination of N-chlorosulfonamides (NCSs) is reported. This remote C(sp3)–H functionalization can be achieved in weak basic solution at room temperature with as little as 0.1 mol % of a photocatalyst. A variety of nitrogen-containing heterocycles (up to 94% yield) and chlorides (up to 93% yield) are prepared from NCSs. Late-stage C(sp3)–H functionalization of complex and biologically important (−)-cis-myrtanylamine and (+)-dehydroabietylamine derivatives can also be achieved with excellent yields and regioselectivity.
Co-reporter:Jiajia Guo and Shouyun Yu
Organic & Biomolecular Chemistry 2015 vol. 13(Issue 4) pp:1179-1186
Publication Date(Web):14 Nov 2014
DOI:10.1039/C4OB02227K
An efficient and enantioselective strategy to synthesize benzoindolizidines from α,β-unsaturated amino ketones via domino intramolecular aza-Michael addition/alkylation was developed. These reactions were enabled by cinchona alkaloid-derived quaternary ammonium salts as the phase-transfer catalyst. A variety of benzoindolizidines were prepared in good yields (up to 93%) and enantioselectivities (up to 92.8:7.2 er).
Co-reporter:Qixue Qin, Daan Ren and Shouyun Yu
Organic & Biomolecular Chemistry 2015 vol. 13(Issue 41) pp:10295-10298
Publication Date(Web):21 Sep 2015
DOI:10.1039/C5OB01725D
A visible-light-promoted chloramination of olefins is reported. N-Chlorosulfonamides serve as both nitrogen and chlorine sources. These reactions provide a simple, efficient, regioselective, and atom-economical method for the preparation of vicinal haloamine derivatives under mild reaction conditions. A variety of olefins were tolerated, and chloramination products were obtained in good yields.
Co-reporter:Heng Jiang, Yuanzheng Cheng, Ruzhi Wang, Yan Zhang and Shouyun Yu
Chemical Communications 2014 vol. 50(Issue 46) pp:6164-6167
Publication Date(Web):15 Apr 2014
DOI:10.1039/C4CC01122H
A synthetic strategy for multi-substituted isoquinoline derivatives has been developed using visible light-promoted vinyl isocyanide insertion with diaryliodonium salts at room temperature. The methodology presented here represents the first example of isoquinoline synthesis via somophilic isocyanide insertion.
Co-reporter:Xiaoyang Sun and Shouyun Yu
Organic Letters 2014 Volume 16(Issue 11) pp:2938-2941
Publication Date(Web):May 21, 2014
DOI:10.1021/ol501081h
A practical and unified strategy has been described for the preparation of mono- and difluoromethylated phenanthridine derivatives using a visible-light-promoted alkylation and decarboxylation sequence from biphenyl isocyanides with ethyl bromofluoroacetate (EBFA) or ethyl bromodifluoroacetate (EBDFA). These reactions could be carried out at room temperature in good to excellent chemical yields. Both stepwise and one-pot procedures have been developed, which makes this strategy more attractive.
Co-reporter:Qixue Qin and Shouyun Yu
Organic Letters 2014 Volume 16(Issue 13) pp:3504-3507
Publication Date(Web):June 25, 2014
DOI:10.1021/ol501457s
A room temperature redox neutral direct C–H amidation of heteroarenes has been achieved. Hydroxylamine derivatives, which are easily accessed, have been employed as tunable nitrogen sources. These reactions were enabled by a visible-light-promoted single-electron transfer pathway without a directing group. A variety of heteroarenes, such as indoles, pyrroles, and furans, could go through this amidation with high yields (up to 98%). These reactions are highly regioselective, and all the products were isolated as a single regioisomer.
Co-reporter:Yuanzheng Cheng;Xiangai Yuan;Heng Jiang;Ruzhi Wang;Jing Ma;Yan Zhang
Advanced Synthesis & Catalysis 2014 Volume 356( Issue 13) pp:2859-2866
Publication Date(Web):
DOI:10.1002/adsc.201400504
Co-reporter:Shuanghua Cheng;Lili Zhao
Advanced Synthesis & Catalysis 2014 Volume 356( Issue 5) pp:982-986
Publication Date(Web):
DOI:10.1002/adsc.201300920
Co-reporter:Jiajia Guo, Xiaoyang Sun and Shouyun Yu
Organic & Biomolecular Chemistry 2014 vol. 12(Issue 2) pp:265-268
Publication Date(Web):30 Oct 2013
DOI:10.1039/C3OB42068J
An efficient and diastereoselective strategy based on an intramolecular domino aza-Michael/Darzens reaction to synthesize epoxide-fused benzoquinolizidines has been described. Three bonds (1 C–C, 1 C–N and 1 C–O), three rings and three chiral centers can be constructed in a single pot under very mild conditions. All the products were isolated in only one diastereomer with 40–80% yields.
Co-reporter:Shuanghua Cheng and Shouyun Yu
Organic & Biomolecular Chemistry 2014 vol. 12(Issue 43) pp:8607-8610
Publication Date(Web):12 Sep 2014
DOI:10.1039/C4OB01646G
A highly enantioselective intramolecular 6-exo-trig aza-Michael addition was developed to afford chiral 3-substituted 1,2-oxazinanes in high yields (up to 99% yield) and good enantioselectivities (up to 98/2 er). These reactions were enabled by a quinine-derived primary–tertiary diamine as a catalyst and pentafluoropropionic acid (PFP) as a co-catalyst.
Co-reporter:Xiaoyang Sun;Jiahong Li;Yunpeng Ni;Daan Ren;Zhentao Hu;Dr. Shouyun Yu
Asian Journal of Organic Chemistry 2014 Volume 3( Issue 12) pp:1317-1325
Publication Date(Web):
DOI:10.1002/ajoc.201402222
Abstract
A practical and environmentally friendly strategy for the preparation of fused quinoline and quinoxaline derivatives has been developed, enabled by domino radical triple bond insertions. These reactions have very high regioselectivity and can be carried out under mild conditions in good to excellent chemical yields.
Co-reporter:Yuanzheng Cheng, Heng Jiang, Yan Zhang, and Shouyun Yu
Organic Letters 2013 Volume 15(Issue 21) pp:5520-5523
Publication Date(Web):October 15, 2013
DOI:10.1021/ol4026827
A mechanistically new strategy has been described for the simple, practical, and environmentally friendly preparation of 6-(trifluoromethyl)phenanthridine derivatives using ionic isocyanide insertion from biphenyl isocyanide derivatives and Umemoto’s reagent. These reactions were promoted only by inorganic base in good-to-excellent chemical yields without any external stoichiometric oxidants and radical initiators.
Co-reporter:Heng Jiang, Yuanzheng Cheng, Yan Zhang, and Shouyun Yu
Organic Letters 2013 Volume 15(Issue 18) pp:4884-4887
Publication Date(Web):September 3, 2013
DOI:10.1021/ol402325z
A conceptually new strategy has been described for the mild, practical, and environmentally friendly preparation of naphthols and furans using a visible-light promoted photoredox neutral approach. These reactions between accessible electron-deficient bromides and commercially available alkynes could be carried out at room temperature in good-to-excellent chemical yields without any external stoichiometric oxidants.
Co-reporter:Heng Jiang;Xuejiao Chen;Yan Zhang
Advanced Synthesis & Catalysis 2013 Volume 355( Issue 4) pp:809-813
Publication Date(Web):
DOI:10.1002/adsc.201200874
Abstract
A mild, practical and environmentally friendly strategy to prepare β-amidovinyl sulfones has been developed based on the sulfonation of enamides or enecarbamates via visible-light photoredox catalysis. Direct CH functionalizations of enamides or enecarbamates under the optimized conditions proceeded with a wide scope of substrates and remarkable selectivity to give functionalized vinyl sulfones with good to excellent yields.
Co-reporter:Hanbin Liu, Chuanqi Zeng, Jiajia Guo, Mengyao Zhang and Shouyun Yu
RSC Advances 2013 vol. 3(Issue 6) pp:1666-1668
Publication Date(Web):04 Dec 2012
DOI:10.1039/C2RA22374K
A highly enantioselective intramolecular aza-Michael addition with enone carbamates catalyzed by chiral Brønsted acids was developed. A domino cross metathesis/aza-Michael addition for the preparation of 2-substituted pyrrolidines or benzopyrrolidines was also explored. The reactions described here provide an efficient asymmetric protocol for enantio-enriched heterocycles, especially 2-substituted pyrrolidines.
Co-reporter:Heng Jiang;Yuanzheng Cheng;Ruzhi Wang;Mengmeng Zheng;Dr. Yan Zhang;Dr. Shouyun Yu
Angewandte Chemie International Edition 2013 Volume 52( Issue 50) pp:13289-13292
Publication Date(Web):
DOI:10.1002/anie.201308376
Co-reporter:Heng Jiang;Yuanzheng Cheng;Ruzhi Wang;Mengmeng Zheng;Dr. Yan Zhang;Dr. Shouyun Yu
Angewandte Chemie 2013 Volume 125( Issue 50) pp:13531-13534
Publication Date(Web):
DOI:10.1002/ange.201308376
Co-reporter:Fengtao Zhou ; Jiajia Guo ; Jianguang Liu ; Ke Ding ; Shouyun Yu ;Qian Cai
Journal of the American Chemical Society 2012 Volume 134(Issue 35) pp:14326-14329
Publication Date(Web):August 22, 2012
DOI:10.1021/ja306631z
The first highly enantioselective copper-catalyzed intramolecular Ullmann C–N coupling reaction has been developed. The asymmetric desymmetrization of 1,3-bis(2-iodoaryl)propan-2-amines catalyzed by CuI/(R)-BINOL-derived ligands led to the enantioselective formation of indolines in high yields and excellent enantiomeric excesses. This method was also applied to the formation of 1,2,3,4-tetrahydroquinolines in high yields and excellent enantioselectivity.
Co-reporter:Heng Jiang;Chengmei Huang;Jiajia Guo;Chuanqi Zeng;Dr. Yan Zhang;Dr. Shouyun Yu
Chemistry - A European Journal 2012 Volume 18( Issue 47) pp:15158-15166
Publication Date(Web):
DOI:10.1002/chem.201201716
Abstract
Direct CH functionalization of various enamides and enecarbamates was realized through visible-light photoredox catalyzed reactions. Under the optimized conditions using [Ir(ppy)2(dtbbpy)PF6] as photocatalyst in combination with Na2HPO4, enamides such as N-vinylpyrrolidinone could be easily functionalized by irradiation of the reaction mixture overnight in acetonitrile with visible light. The scope of the reaction with respect to enamide and enecarbamate substrates by using diethyl 2-bromomalonate for the alkylation reaction was explored, followed by an investigation of the scope of alkylating reagents used to react with the enamides and enecarbamates. The results indicated that reaction takes place with quite broad substrate scope, however, tertiary enamides with an internal CC double bond in the E configuration could not be alkylated. Alkylation of N-vinyl tertiary enamides and enecarbamates gave monoalkylated products exclusively in the E configuration. Alkylation of N-vinyl secondary enamides gave doubly alkylated products. Double bond migration was observed in the reaction of electron-deficient bromides such as 3-bromoacetyl acetate with N-vinylpyrrolidinone. A mechanism is proposed for the reaction that is different from reported reactions of SOMOphiles with a nonfunctionalized CC double bond. Further tests on the trifluoromethylation and arylation of enamides and enecarbamates under similar conditions showed that the reactions could serve as a mild, practical, and environmentally friendly approach to various functionalized enamides and enecarbamates.
Co-reporter:Xiao-De An
Organic Letters () pp:
Publication Date(Web):September 29, 2015
DOI:10.1021/acs.orglett.5b02547
The direct synthesis of nitriles from commercially available or easily prepared aldehydes has been achieved. O-(4-CF3-benzoyl)-hydroxylamine (CF3-BHA) was utilized as the nitrogen source to generate O-acyl oximes in situ with aldehydes, which can be converted to a nitrile with the assistance of a Brønsted acid. Several aliphatic, aromatic, and α,β-unsaturated nitriles that contain different functional groups were prepared in high yields (up to 94% yield). This method has notable advantages, such as simple and mild conditions, high yields, and good functional group tolerance.
Co-reporter:Xiaoyang Sun and Shouyun Yu
Chemical Communications 2016 - vol. 52(Issue 72) pp:NaN10901-10901
Publication Date(Web):2016/08/09
DOI:10.1039/C6CC05756J
An efficient strategy assisted by visible-light-promoted iminyl radical formation has been developed for the synthesis of 6-(fluoro)alkylated phenanthridine derivatives. In the reactions, addition of alkyl and trifluoromethyl radicals onto vinyl azides gives iminyl radicals, which then undergo intramolecular homolytic aromatic substitution leading to phenanthridines. These reactions can be carried out under mild conditions with high chemical yields and broad substrate scope.
Co-reporter:Xiaodong Liu, Kun Tong, Ai Hua Zhang, Ren Xiang Tan and Shouyun Yu
Inorganic Chemistry Frontiers 2017 - vol. 4(Issue 7) pp:
Publication Date(Web):
DOI:10.1039/C7QO00199A
Co-reporter:Yue-Yue Han, Hao Wang and Shouyun Yu
Inorganic Chemistry Frontiers 2016 - vol. 3(Issue 8) pp:NaN956-956
Publication Date(Web):2016/06/07
DOI:10.1039/C6QO00116E
A novel approach has been reported for the preparation of biaryl sultams using visible-light-promoted denitrogenative cyclization of 1,2,3,4-benzothiatriazine-1,1-dioxides. A variety of biaryl sultams have been prepared with the assistance of a photocatalyst under visible light at room temperature with satisfactory yields. Both stepwise and one-pot procedures have been developed, thus improving the practicability of this synthetic strategy.
Co-reporter:Heng Jiang, Yuanzheng Cheng, Ruzhi Wang, Yan Zhang and Shouyun Yu
Chemical Communications 2014 - vol. 50(Issue 46) pp:NaN6167-6167
Publication Date(Web):2014/04/15
DOI:10.1039/C4CC01122H
A synthetic strategy for multi-substituted isoquinoline derivatives has been developed using visible light-promoted vinyl isocyanide insertion with diaryliodonium salts at room temperature. The methodology presented here represents the first example of isoquinoline synthesis via somophilic isocyanide insertion.
Co-reporter:Hui Zhou, Xinzhao Deng, Zhenjun Ma, Aihua Zhang, Qixue Qin, Ren Xiang Tan and Shouyun Yu
Organic & Biomolecular Chemistry 2016 - vol. 14(Issue 25) pp:NaN6070-6070
Publication Date(Web):2016/05/18
DOI:10.1039/C6OB00768F
The synthesis of privileged structures, which are potent drug candidates, is an impetus for drug discovery. The construction of heterocyclic framework furo[3,2-c]coumarins using a visible-light promoted photoredox neutral coupling of 3-bromo-4-hydroxycoumarins with commercially available alkynes has been reported. These reactions can be carried out at room temperature under visible light irradiation with good chemical yields. This work presents 17 furocoumarins, 12 of which are new. Three of the newly synthesized compounds show potent cytotoxicity, and one shows moderate acetylcholinesterase inhibitory activity with IC50 values of 2.16 ± 0.13 μM.
Co-reporter:Qixue Qin, Daan Ren and Shouyun Yu
Organic & Biomolecular Chemistry 2015 - vol. 13(Issue 41) pp:NaN10298-10298
Publication Date(Web):2015/09/21
DOI:10.1039/C5OB01725D
A visible-light-promoted chloramination of olefins is reported. N-Chlorosulfonamides serve as both nitrogen and chlorine sources. These reactions provide a simple, efficient, regioselective, and atom-economical method for the preparation of vicinal haloamine derivatives under mild reaction conditions. A variety of olefins were tolerated, and chloramination products were obtained in good yields.
Co-reporter:Jiajia Guo and Shouyun Yu
Organic & Biomolecular Chemistry 2015 - vol. 13(Issue 4) pp:NaN1186-1186
Publication Date(Web):2014/11/14
DOI:10.1039/C4OB02227K
An efficient and enantioselective strategy to synthesize benzoindolizidines from α,β-unsaturated amino ketones via domino intramolecular aza-Michael addition/alkylation was developed. These reactions were enabled by cinchona alkaloid-derived quaternary ammonium salts as the phase-transfer catalyst. A variety of benzoindolizidines were prepared in good yields (up to 93%) and enantioselectivities (up to 92.8:7.2 er).
Co-reporter:Jiajia Guo, Xiaoyang Sun and Shouyun Yu
Organic & Biomolecular Chemistry 2014 - vol. 12(Issue 2) pp:NaN268-268
Publication Date(Web):2013/10/30
DOI:10.1039/C3OB42068J
An efficient and diastereoselective strategy based on an intramolecular domino aza-Michael/Darzens reaction to synthesize epoxide-fused benzoquinolizidines has been described. Three bonds (1 C–C, 1 C–N and 1 C–O), three rings and three chiral centers can be constructed in a single pot under very mild conditions. All the products were isolated in only one diastereomer with 40–80% yields.
Co-reporter:Shuanghua Cheng and Shouyun Yu
Organic & Biomolecular Chemistry 2014 - vol. 12(Issue 43) pp:NaN8610-8610
Publication Date(Web):2014/09/12
DOI:10.1039/C4OB01646G
A highly enantioselective intramolecular 6-exo-trig aza-Michael addition was developed to afford chiral 3-substituted 1,2-oxazinanes in high yields (up to 99% yield) and good enantioselectivities (up to 98/2 er). These reactions were enabled by a quinine-derived primary–tertiary diamine as a catalyst and pentafluoropropionic acid (PFP) as a co-catalyst.
![Dinaphtho[2,1-d:1',2'-f][1,3,2]dioxaphosphepin,4-hydroxy-2,6-bis[2,4,6-tris(1-methylethyl)phenyl]-, 4-oxide, (11bR)-](/data/chemimg/115800/791616-63-2.png)
![Dinaphtho[2,1-d:1',2'-f][1,3,2]dioxaphosphepin,4-hydroxy-2,6-bis[2,4,6-tris(1-methylethyl)phenyl]-, 4-oxide, (11bR)-](/data/chemimg/115800/791616-63-2_b.png)
![9H-Phenanthro[9,10-b]quinolizine, 11,12,13,14,14a,15-hexahydro-3,6,7-trimethoxy-, (14aR)-](/data/chemimg/103200/666175-37-7.png)
![9H-Phenanthro[9,10-b]quinolizine, 11,12,13,14,14a,15-hexahydro-3,6,7-trimethoxy-, (14aR)-](/data/chemimg/103200/666175-37-7_b.png)
![Ethanone, 1-(4-fluorophenyl)-2-[(4-methylphenyl)sulfonyl]-](http://img.cochemist.com/ccimg/189200/189108-49-4.png)
![Ethanone, 1-(4-fluorophenyl)-2-[(4-methylphenyl)sulfonyl]-](http://img.cochemist.com/ccimg/189200/189108-49-4_b.png)
![1(2H)-Naphthalenone, 3,4-dihydro-2-[(4-methylphenyl)sulfonyl]-](/data/chemimg/128900/165591-56-0.png)
![1(2H)-Naphthalenone, 3,4-dihydro-2-[(4-methylphenyl)sulfonyl]-](/data/chemimg/128900/165591-56-0_b.png)
![Benzene, 1-chloro-4-[[(trifluoromethyl)sulfonyl]ethynyl]-](http://img.cochemist.com/ccimg/150700/150619-48-0.png)
![Benzene, 1-chloro-4-[[(trifluoromethyl)sulfonyl]ethynyl]-](http://img.cochemist.com/ccimg/150700/150619-48-0_b.png)
![Ethanone, 2-([1,1'-biphenyl]-4-ylsulfonyl)-1-phenyl-](http://img.cochemist.com/ccimg/130200/130188-81-7.png)
![Ethanone, 2-([1,1'-biphenyl]-4-ylsulfonyl)-1-phenyl-](http://img.cochemist.com/ccimg/130200/130188-81-7_b.png)
![BUTANOIC ACID, 4-[[(4-METHYLPHENYL)SULFONYL]AMINO]-, METHYL ESTER](http://img.cochemist.com/ccimg/118500/118429-43-9.png)
![BUTANOIC ACID, 4-[[(4-METHYLPHENYL)SULFONYL]AMINO]-, METHYL ESTER](http://img.cochemist.com/ccimg/118500/118429-43-9_b.png)
![2-Oxazolidinone, 3-[(1E)-2-phenylethenyl]-](http://img.cochemist.com/ccimg/112600/112518-17-9.png)
![2-Oxazolidinone, 3-[(1E)-2-phenylethenyl]-](http://img.cochemist.com/ccimg/112600/112518-17-9_b.png)
![Silane, (1,1-dimethylethyl)dimethyl[(1-phenyl-1-propenyl)oxy]-](http://img.cochemist.com/ccimg/94300/94287-27-1.png)
![Silane, (1,1-dimethylethyl)dimethyl[(1-phenyl-1-propenyl)oxy]-](http://img.cochemist.com/ccimg/94300/94287-27-1_b.png)
![Carbamic acid, [2-(2-propenyl)phenyl]-, phenylmethyl ester](http://img.cochemist.com/ccimg/86200/86136-89-2.png)
![Carbamic acid, [2-(2-propenyl)phenyl]-, phenylmethyl ester](http://img.cochemist.com/ccimg/86200/86136-89-2_b.png)
![Silane, (1,1-dimethylethyl)dimethyl[(1-phenylethenyl)oxy]-](http://img.cochemist.com/ccimg/66400/66324-10-5.png)
![Silane, (1,1-dimethylethyl)dimethyl[(1-phenylethenyl)oxy]-](http://img.cochemist.com/ccimg/66400/66324-10-5_b.png)
![Ethanone, 1-(4-chlorophenyl)-2-[(4-methylphenyl)sulfonyl]-](http://img.cochemist.com/ccimg/61900/61820-94-8.png)
![Ethanone, 1-(4-chlorophenyl)-2-[(4-methylphenyl)sulfonyl]-](http://img.cochemist.com/ccimg/61900/61820-94-8_b.png)
![Benzene,[2-[(trifluoromethyl)sulfonyl]ethynyl]-](http://img.cochemist.com/ccimg/52900/52843-77-3.png)
![Benzene,[2-[(trifluoromethyl)sulfonyl]ethynyl]-](http://img.cochemist.com/ccimg/52900/52843-77-3_b.png)
![BENZENESULFONIC ACID, [(4-METHYLPHENYL)METHYLENE]HYDRAZIDE](http://img.cochemist.com/ccimg/50700/50626-25-0.png)
![BENZENESULFONIC ACID, [(4-METHYLPHENYL)METHYLENE]HYDRAZIDE](http://img.cochemist.com/ccimg/50700/50626-25-0_b.png)
![ETHANONE, 2-[(4-METHOXYPHENYL)SULFONYL]-1-PHENYL-](http://img.cochemist.com/ccimg/41100/41024-54-8.png)
![ETHANONE, 2-[(4-METHOXYPHENYL)SULFONYL]-1-PHENYL-](http://img.cochemist.com/ccimg/41100/41024-54-8_b.png)
![ETHANONE, 2-[(4-NITROPHENYL)SULFONYL]-1-PHENYL-](http://img.cochemist.com/ccimg/41100/41024-48-0.png)
![ETHANONE, 2-[(4-NITROPHENYL)SULFONYL]-1-PHENYL-](http://img.cochemist.com/ccimg/41100/41024-48-0_b.png)
![Ethanone,1-(4-bromophenyl)-2-[(4-methylphenyl)sulfonyl]-](http://img.cochemist.com/ccimg/31400/31377-97-6.png)
![Ethanone,1-(4-bromophenyl)-2-[(4-methylphenyl)sulfonyl]-](http://img.cochemist.com/ccimg/31400/31377-97-6_b.png)
![METHYL 1-AZABICYCLO[2.2.2]OCT-2-ENE-3-CARBOXYLATE](http://img.cochemist.com/ccimg/30500/30418-53-2.png)
![METHYL 1-AZABICYCLO[2.2.2]OCT-2-ENE-3-CARBOXYLATE](http://img.cochemist.com/ccimg/30500/30418-53-2_b.png)
![2-[(4-methylphenyl)sulfonyl]-1-phenylpropan-1-one](http://img.cochemist.com/ccimg/14200/14195-15-4.png)
![2-[(4-methylphenyl)sulfonyl]-1-phenylpropan-1-one](http://img.cochemist.com/ccimg/14200/14195-15-4_b.png)
![N-[2-(3,4-DIMETHOXYPHENYL)ETHYL]-4-METHYLBENZENESULFONAMIDE](http://img.cochemist.com/data/images/14165-67-4.png)
![N-[2-(3,4-DIMETHOXYPHENYL)ETHYL]-4-METHYLBENZENESULFONAMIDE](http://img.cochemist.com/data/images/14165-67-4_b.png)
![9H-Phenanthro[9,10-b]quinolizine,11,12,13,14,14a,15-hexahydro-2,3,6-trimethoxy-, (14aR)-](http://img.cochemist.com/ccimg/500/482-22-4.png)
![9H-Phenanthro[9,10-b]quinolizine,11,12,13,14,14a,15-hexahydro-2,3,6-trimethoxy-, (14aR)-](http://img.cochemist.com/ccimg/500/482-22-4_b.png)
![PHENANTHRIDINE, 6-[4-(TRIFLUOROMETHYL)PHENYL]-](http://img.cochemist.com/ccimg/880500/880493-15-2.png)
![PHENANTHRIDINE, 6-[4-(TRIFLUOROMETHYL)PHENYL]-](http://img.cochemist.com/ccimg/880500/880493-15-2_b.png)
![BENZO[H]QUINOLINE-3-CARBOXYLIC ACID, 2-METHYL-, ETHYL ESTER](http://img.cochemist.com/ccimg/879900/879895-04-2.png)
![BENZO[H]QUINOLINE-3-CARBOXYLIC ACID, 2-METHYL-, ETHYL ESTER](http://img.cochemist.com/ccimg/879900/879895-04-2_b.png)
![[1,1'-Biphenyl]-4-carbonitrile, 2'-acetyl-](http://img.cochemist.com/ccimg/858100/858035-57-1.png)
![[1,1'-Biphenyl]-4-carbonitrile, 2'-acetyl-](http://img.cochemist.com/ccimg/858100/858035-57-1_b.png)
![Benzenesulfonamide, 4-methyl-N-[2-(phenylmethoxy)ethyl]-](http://img.cochemist.com/ccimg/604000/603986-07-8.png)
![Benzenesulfonamide, 4-methyl-N-[2-(phenylmethoxy)ethyl]-](http://img.cochemist.com/ccimg/604000/603986-07-8_b.png)
![Benzenesulfonamide, 2-nitro-N-[4-(trifluoromethyl)phenyl]-](http://img.cochemist.com/ccimg/501200/501120-68-9.png)
![Benzenesulfonamide, 2-nitro-N-[4-(trifluoromethyl)phenyl]-](http://img.cochemist.com/ccimg/501200/501120-68-9_b.png)
![1,2,3-Benzotriazin-4(3H)-one, 3-[4-(trifluoromethyl)phenyl]-](http://img.cochemist.com/ccimg/367300/367249-03-4.png)
![1,2,3-Benzotriazin-4(3H)-one, 3-[4-(trifluoromethyl)phenyl]-](http://img.cochemist.com/ccimg/367300/367249-03-4_b.png)
![1-([1,1'-Biphenyl]-2-yl)-2-phenylethanone](http://img.cochemist.com/ccimg/230000/229970-97-2.png)
![1-([1,1'-Biphenyl]-2-yl)-2-phenylethanone](http://img.cochemist.com/ccimg/230000/229970-97-2_b.png)
![Ethanone,1-(4'-methoxy[1,1'-biphenyl]-2-yl)-](http://img.cochemist.com/ccimg/192900/192863-43-7.png)
![Ethanone,1-(4'-methoxy[1,1'-biphenyl]-2-yl)-](http://img.cochemist.com/ccimg/192900/192863-43-7_b.png)
![Butanoic acid, 2-[(4-bromophenyl)methylene]-3-oxo-, ethyl ester](/data/chemimg/130800/186682-26-8.png)
![Butanoic acid, 2-[(4-bromophenyl)methylene]-3-oxo-, ethyl ester](/data/chemimg/130800/186682-26-8_b.png)
![Boronic acid, [(1Z)-1-methyl-2-phenylethenyl]-](http://img.cochemist.com/ccimg/174900/174836-34-1.png)
![Boronic acid, [(1Z)-1-methyl-2-phenylethenyl]-](http://img.cochemist.com/ccimg/174900/174836-34-1_b.png)
![[1,1-Biphenyl]-4-methanol, α-ethenyl-](/data/chemimg/3765700/170938-13-3.png)
![[1,1-Biphenyl]-4-methanol, α-ethenyl-](/data/chemimg/3765700/170938-13-3_b.png)
![Piperidine, 1-[2-(formylamino)-1-oxo-3,3-diphenyl-2-propenyl]-](http://img.cochemist.com/ccimg/120400/120302-02-5.png)
![Piperidine, 1-[2-(formylamino)-1-oxo-3,3-diphenyl-2-propenyl]-](http://img.cochemist.com/ccimg/120400/120302-02-5_b.png)
![6H-Dibenzo[c,e][1,2]thiazine, 7-methoxy-, 5,5-dioxide](http://img.cochemist.com/ccimg/117600/117562-04-6.png)
![6H-Dibenzo[c,e][1,2]thiazine, 7-methoxy-, 5,5-dioxide](http://img.cochemist.com/ccimg/117600/117562-04-6_b.png)
![1H-Pyrrole, 2-[4-(trifluoromethyl)phenyl]-](http://img.cochemist.com/ccimg/115500/115464-88-5.png)
![1H-Pyrrole, 2-[4-(trifluoromethyl)phenyl]-](http://img.cochemist.com/ccimg/115500/115464-88-5_b.png)
![Methanone, [1,1'-biphenyl]-2-yl(4-chlorophenyl)-](http://img.cochemist.com/ccimg/113500/113449-33-5.png)
![Methanone, [1,1'-biphenyl]-2-yl(4-chlorophenyl)-](http://img.cochemist.com/ccimg/113500/113449-33-5_b.png)
![Isoindolo[1,2-b]quinazolin-10(12H)-one](http://img.cochemist.com/ccimg/109500/109439-60-3.png)
![Isoindolo[1,2-b]quinazolin-10(12H)-one](http://img.cochemist.com/ccimg/109500/109439-60-3_b.png)
![Acetamide, N-[3-(4-pentenyloxy)phenyl]-](http://img.cochemist.com/ccimg/107200/107195-49-3.png)
![Acetamide, N-[3-(4-pentenyloxy)phenyl]-](http://img.cochemist.com/ccimg/107200/107195-49-3_b.png)
![Benzoic acid, 4-[[(2-aminophenyl)sulfonyl]amino]-, methyl ester](http://img.cochemist.com/ccimg/102000/101954-57-8.png)
![Benzoic acid, 4-[[(2-aminophenyl)sulfonyl]amino]-, methyl ester](http://img.cochemist.com/ccimg/102000/101954-57-8_b.png)
![L-Isoleucine, N-[(4-methylphenyl)sulfonyl]-, methyl ester](http://img.cochemist.com/ccimg/95400/95305-52-5.png)
![L-Isoleucine, N-[(4-methylphenyl)sulfonyl]-, methyl ester](http://img.cochemist.com/ccimg/95400/95305-52-5_b.png)
![1-Propanone, 1-[1,1'-biphenyl]-2-yl-](http://img.cochemist.com/ccimg/92600/92548-82-8.png)
![1-Propanone, 1-[1,1'-biphenyl]-2-yl-](http://img.cochemist.com/ccimg/92600/92548-82-8_b.png)
![Pyrrolidine, 3-methyl-1-[(4-methylphenyl)sulfonyl]-](/data/chemimg/964400/86553-37-9.png)
![Pyrrolidine, 3-methyl-1-[(4-methylphenyl)sulfonyl]-](/data/chemimg/964400/86553-37-9_b.png)
![Benzene, [(bromodifluoromethyl)sulfonyl]-](http://img.cochemist.com/ccimg/80400/80351-58-2.png)
![Benzene, [(bromodifluoromethyl)sulfonyl]-](http://img.cochemist.com/ccimg/80400/80351-58-2_b.png)
![6H-DIBENZO[C,E][1,2]THIAZINE, 9-METHOXY-, 5,5-DIOXIDE](http://img.cochemist.com/ccimg/65700/65645-69-4.png)
![6H-DIBENZO[C,E][1,2]THIAZINE, 9-METHOXY-, 5,5-DIOXIDE](http://img.cochemist.com/ccimg/65700/65645-69-4_b.png)
![Benzene, [(5-hexenyloxy)methyl]-](http://img.cochemist.com/ccimg/59200/59137-50-7.png)
![Benzene, [(5-hexenyloxy)methyl]-](http://img.cochemist.com/ccimg/59200/59137-50-7_b.png)
![8H-Isoquino[1,2-b]quinazolin-8-one, 5,6-dihydro-](http://img.cochemist.com/ccimg/57100/57098-81-4.png)
![8H-Isoquino[1,2-b]quinazolin-8-one, 5,6-dihydro-](http://img.cochemist.com/ccimg/57100/57098-81-4_b.png)
![Benzo[i]phenanthridine, 5-phenyl-](http://img.cochemist.com/ccimg/54700/54607-46-4.png)
![Benzo[i]phenanthridine, 5-phenyl-](http://img.cochemist.com/ccimg/54700/54607-46-4_b.png)
![Acetamide, N-[2-(5-methoxy-1-methyl-1H-indol-3-yl)ethyl]-](http://img.cochemist.com/ccimg/53400/53350-25-7.png)
![Acetamide, N-[2-(5-methoxy-1-methyl-1H-indol-3-yl)ethyl]-](http://img.cochemist.com/ccimg/53400/53350-25-7_b.png)
![2-Propen-1-one, 1-[1,1'-biphenyl]-4-yl-](http://img.cochemist.com/ccimg/42600/42575-11-1.png)
![2-Propen-1-one, 1-[1,1'-biphenyl]-4-yl-](http://img.cochemist.com/ccimg/42600/42575-11-1_b.png)
![CARBAMIC ACID, [2-(1H-INDOL-3-YL)ETHYL]-, PHENYLMETHYL ESTER](http://img.cochemist.com/ccimg/38800/38750-13-9.png)
![CARBAMIC ACID, [2-(1H-INDOL-3-YL)ETHYL]-, PHENYLMETHYL ESTER](http://img.cochemist.com/ccimg/38800/38750-13-9_b.png)
![Leucomycin V,9-O-[(2R,5S,6R)-5-(dimethylamino)tetrahydro-6-methyl-2H-pyran-2-yl]-](http://img.cochemist.com/ccimg/25000/24916-50-5.png)
![Leucomycin V,9-O-[(2R,5S,6R)-5-(dimethylamino)tetrahydro-6-methyl-2H-pyran-2-yl]-](http://img.cochemist.com/ccimg/25000/24916-50-5_b.png)
![Pyrrolidine, 1-[(4-methylphenyl)sulfonyl]-2-phenyl-](http://img.cochemist.com/ccimg/24600/24517-59-7.png)
![Pyrrolidine, 1-[(4-methylphenyl)sulfonyl]-2-phenyl-](http://img.cochemist.com/ccimg/24600/24517-59-7_b.png)
![Butanoic acid, 2-[(4-chlorophenyl)methylene]-3-oxo-, ethyl ester](http://img.cochemist.com/ccimg/19500/19411-80-4.png)
![Butanoic acid, 2-[(4-chlorophenyl)methylene]-3-oxo-, ethyl ester](http://img.cochemist.com/ccimg/19500/19411-80-4_b.png)
![2,3-dimethoxy[1,3]benzodioxolo[5,6-c]phenanthridine](http://img.cochemist.com/ccimg/18100/18034-03-2.png)
![2,3-dimethoxy[1,3]benzodioxolo[5,6-c]phenanthridine](http://img.cochemist.com/ccimg/18100/18034-03-2_b.png)
![4'-Methyl-[1,1'-biphenyl]-2-carbaldehyde](http://img.cochemist.com/ccimg/16200/16191-28-9.png)
![4'-Methyl-[1,1'-biphenyl]-2-carbaldehyde](http://img.cochemist.com/ccimg/16200/16191-28-9_b.png)
![Butanoic acid, 2-[(4-methoxyphenyl)methylene]-3-oxo-, ethyl ester](http://img.cochemist.com/ccimg/15800/15725-26-5.png)
![Butanoic acid, 2-[(4-methoxyphenyl)methylene]-3-oxo-, ethyl ester](http://img.cochemist.com/ccimg/15800/15725-26-5_b.png)
![Butanoic acid, 2-[(3-methoxyphenyl)methylene]-3-oxo-, ethyl ester](http://img.cochemist.com/ccimg/15800/15725-25-4.png)
![Butanoic acid, 2-[(3-methoxyphenyl)methylene]-3-oxo-, ethyl ester](http://img.cochemist.com/ccimg/15800/15725-25-4_b.png)
![Butanoic acid, 2-[(3-chlorophenyl)methylene]-3-oxo-, ethyl ester](http://img.cochemist.com/ccimg/15800/15725-23-2.png)
![Butanoic acid, 2-[(3-chlorophenyl)methylene]-3-oxo-, ethyl ester](http://img.cochemist.com/ccimg/15800/15725-23-2_b.png)
![3-[(5Z)-5-(2,5-DIMETHOXYBENZYLIDENE)-4-OXO-2-THIOXO-1,3-THIAZOLID<WBR />IN-3-YL]PROPANOIC ACID](http://img.cochemist.com/ccimg/7700/7691-76-1.png)
![3-[(5Z)-5-(2,5-DIMETHOXYBENZYLIDENE)-4-OXO-2-THIOXO-1,3-THIAZOLID<WBR />IN-3-YL]PROPANOIC ACID](http://img.cochemist.com/ccimg/7700/7691-76-1_b.png)
![PYRROLIDINE, 2-METHYL-1-[(4-METHYLPHENYL)SULFONYL]-](http://img.cochemist.com/ccimg/6500/6435-79-6.png)
![PYRROLIDINE, 2-METHYL-1-[(4-METHYLPHENYL)SULFONYL]-](http://img.cochemist.com/ccimg/6500/6435-79-6_b.png)
![Acetamide, N-[2-(bromoacetyl)phenyl]-](http://img.cochemist.com/ccimg/4700/4688-64-6.png)
![Acetamide, N-[2-(bromoacetyl)phenyl]-](http://img.cochemist.com/ccimg/4700/4688-64-6_b.png)
![[1,1':4',1''-Terphenyl]-2-carboxaldehyde](http://img.cochemist.com/ccimg/3400/3365-13-7.png)
![[1,1':4',1''-Terphenyl]-2-carboxaldehyde](http://img.cochemist.com/ccimg/3400/3365-13-7_b.png)
![Ethanone, 1-[1,1'-biphenyl]-4-yl-2-(triphenylphosphoranylidene)-](http://img.cochemist.com/ccimg/3000/2959-60-6.png)
![Ethanone, 1-[1,1'-biphenyl]-4-yl-2-(triphenylphosphoranylidene)-](http://img.cochemist.com/ccimg/3000/2959-60-6_b.png)
![6H-Dibenzo[c,e][1,2]thiazine, 5,5-dioxide](http://img.cochemist.com/ccimg/1900/1864-33-1.png)
![6H-Dibenzo[c,e][1,2]thiazine, 5,5-dioxide](http://img.cochemist.com/ccimg/1900/1864-33-1_b.png)
![Naphtho[2,3-d]-1,3-dioxole](http://img.cochemist.com/ccimg/300/269-43-2.png)
![Naphtho[2,3-d]-1,3-dioxole](http://img.cochemist.com/ccimg/300/269-43-2_b.png)
![Benzo[c][1,7]naphthyridine](http://img.cochemist.com/ccimg/300/229-88-9.png)
![Benzo[c][1,7]naphthyridine](http://img.cochemist.com/ccimg/300/229-88-9_b.png)
![2,3,8,9-bismethylenedioxybenzo[c]phenanthridine](http://img.cochemist.com/ccimg/300/217-52-7.png)
![2,3,8,9-bismethylenedioxybenzo[c]phenanthridine](http://img.cochemist.com/ccimg/300/217-52-7_b.png)
![benzo[a]phenanthridine](http://img.cochemist.com/ccimg/200/195-29-9.png)
![benzo[a]phenanthridine](http://img.cochemist.com/ccimg/200/195-29-9_b.png)
![1H-Indole, 1-[(4-methoxyphenyl)methyl]-3-methyl-](/data/chemimg/3735200/1616246-59-3.png)
![1H-Indole, 1-[(4-methoxyphenyl)methyl]-3-methyl-](/data/chemimg/3735200/1616246-59-3_b.png)
![4'-Chloro-[1,1'-biphenyl]-2-carbaldehyde](http://img.cochemist.com/ccimg/153900/153850-83-0.png)
![4'-Chloro-[1,1'-biphenyl]-2-carbaldehyde](http://img.cochemist.com/ccimg/153900/153850-83-0_b.png)
![[1,1'-Biphenyl]-2-carboxaldehyde, 4'-acetyl-](http://img.cochemist.com/ccimg/151000/150970-51-7.png)
![[1,1'-Biphenyl]-2-carboxaldehyde, 4'-acetyl-](http://img.cochemist.com/ccimg/151000/150970-51-7_b.png)
![3'-Methoxy-[1,1'-biphenyl]-2-carboxaldehyde](http://img.cochemist.com/ccimg/38500/38491-36-0.png)
![3'-Methoxy-[1,1'-biphenyl]-2-carboxaldehyde](http://img.cochemist.com/ccimg/38500/38491-36-0_b.png)
![[1,1'-Biphenyl]-2-carboxaldehyde,4'-methoxy-](http://img.cochemist.com/ccimg/16100/16064-04-3.png)
![[1,1'-Biphenyl]-2-carboxaldehyde,4'-methoxy-](http://img.cochemist.com/ccimg/16100/16064-04-3_b.png)
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![Ethanone,1-[1,1'-biphenyl]-2-yl-](http://img.cochemist.com/ccimg/2200/2142-66-7_b.png)
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![[1,3]dioxolo[4,5-j]phenanthridine](http://img.cochemist.com/ccimg/300/224-11-3_b.png)
![benzo[c]phenanthridine](http://img.cochemist.com/ccimg/300/218-38-2.png)
![benzo[c]phenanthridine](http://img.cochemist.com/ccimg/300/218-38-2_b.png)
